5 Make-or-Break Questions Nobody's Asking

Great! You’re ready to dive into email list management and start building your new business.


Imagine this: a business owner just reached out, eager for help with their email marketing.


Exciting, right? As a new email list manager, you’re hungry for clients!


But before you dive in headfirst, let’s hit pause for a second.


You’re starting out your part-time business as an email list manager. Chances are, your first set of potential clients know nothing about email. All they know is that “someone” told them they should do it.


And besides, that’s why they want to hire YOU, right?


Asking the right questions upfront is essential to make sure this prospect is a good fit for your growing business. After all, you don’t want to get stuck with someone whose email list is ancient—or worse, bought from a sketchy agency.


I’m going to share five key questions you should ask to qualify new prospects. These questions will help you spot red flags and decide if this client is the real deal.


Think of this list as your go-to guide for starting your new business on the right foot.

Q1: Where Do You Get Your Email Addresses?

Here’s the right answer: the owners of the email addresses have given me permission to send promotional emails to them.


Here’s some variations on the right answer:

  • I was exhibiting at an art show and people wrote their email address down on my sign-up sheet.
  • I have a “Contact Me” form on my website.
  • I have an email address field on my web store’s checkout page.
  • I have a fishbowl on my store counter where people who want my emails drop their business cards in.
  • I have a list of the email addresses of all our students (or their parents).
  • I have a list of everyone in my church who wants to stay informed by email.

Here's a list of Red Flag answers:

  • I bought this list of email addresses from an agency that sells qualified leads for my industry.
  • I went online and copied the email addresses from their business web sites.
  • I bought out a company and these email addresses were on a spreadsheet they had in their office.

Here's Why it Matters

The United States is the only country in the world that allows commercial emails to be sent to people who haven’t given their explicit permission. It’s against the law everywhere else.


Even if the subscribers are all in the U.S., sending emails to people who haven’t given you permission violates every reputable email service provider’s Terms of Use.


Unsolicited emails also mean spam complaints. Mailbox providers have a very low tolerance for spam complaints. Either way, they’ll boot you off their platform faster than a toupee in a West Texas tornado.

Q2: How Long Ago Since You Last Emailed Them?

Here's the right answer: I've sent at least one email in the past 30 days.


Here's some variations on the right answer:

  • I've sent at least one email in the past 60 days.
  • I've not started yet. That's why I want to hire you!

Here's a list of Red Flag answers:

  • Uhhhh ... Wow! I don't remember!
  • The last email was more than 3 months ago.

Here's Why it Matters

People forget who they gave their email address to. Getting an email clear out of the blue from someone they don’t know leads to spam complaints. All it takes is just a few complaints and the mailbox providers will permanently block your emails. Keep getting these complaints and eventually you'll get kicked off your email platform.


That having been said, if you’re starting to send emails for the very first time for your client, then you’ll need to be very deliberate in how you do it.

Q3: How Often Do You Send Emails?

Here's the right answer: I send at least once a week.


Here's some variations on the right answer:

  • I try to send at least once in a 10-14 day period.
  • I haven't started sending yet. What do you suggest?

Here's a list of Red Flag answers:

  • Not regularly – only when I have something to announce.
  • Only when we have a donation drive going on.
  • Not much during the year. We do all our emailing starting with Black Friday through to New Year's Day.

Here's Why it Matters

You want to be sending emails on a regular basis so that your emails will stay fresh in your recipients’ minds. Sending emails once in a while means they’ll quickly forget about you and won’t read your emails. Or worse, they’ll forget that your emails are legit and flag them as spam.


Mailbox providers also look for a regular cadence of email sending. It tells them that you’re not a scam artist who sends a blast of password-stealing fake emails and then skips town. It tells them that you’re a legitimate sender with a legitimate audience who wants your emails.

Q4: Do You Have a Web Site?

Here’s the right answer: Yes, I do, and the root domain of my web site’s URL is the same as the one I use for my emails’ “from address”.


Here’s some variations on the right answer:

  • Yes – I just launched it last month.
  • Not yet. But I’m getting one in the next 30 days.
  • Should I? What do you suggest?

Here's a list of Red Flag answers:

  • Yes, I do – but the root domain of my web site’s URL is different from the one I use for my emails’ “from address”.
  • Not yet; but I’ll have one in about 3 months from now.
  • No, I don’t.
  • I don’t need one.

Here's Why it Matters

The major mailbox providers like Gmail and Yahoo match web site traffic with your email’s “from address”. The more regular the visits to your web site, the more likely they’ll place your emails in the recipient’s inboxes.


A “from address” that doesn’t have a matching web site is a huge red flag to them. To them, your emails look like they came from a scam artist. There’s a high chance they’ll send your emails to the spam folder. Worse, they’ll refuse to accept them.

Q5: When Was the Last Time You Updated Your Web Site?

Here’s the right answer: I’m constantly updating information on my website – sometimes several times a week.


Here’s some variations on the right answer:

  • Not often, but I try to update something at least once a month.
  • I have a web store. My products don’t change that much, but I drive a lot of traffic to my site.

Here's a list of Red Flag answers:

  • Oh – it’s been well over a year since I last updated anything.
  • I just launched my web site last week, so no traffic yet.

Here's Why it Matters

Just because your potential client has a web site doesn’t mean that it’s “real”. Scammers can always fake a web site. But they can’t easily fake traffic to their sites.


Mailbox providers use web site traffic to determine whether your emails are legitimate.


Real web sites always have fresh content. You can always spot a questionable site if none of the pages on their site have been updated in over a year.

The Bottom Line

Resist the temptation to always say "Yes."


I get it.


It's hard to say, "No" when you're just starting out and desparate for business.


Hubris will influence you to think that you can solve everything.


True. My courses that teach you how to be a professional email list manager put you in the expert driver's seat. And yes, you CAN solve just about everything.


Just know beforehand what you're getting yourself into when you do take on their business.


Asking these questions also builds your credibility. Even those business owners who are strong email list managers themselves will appreciate and respect you for taking the time to dive into the details with them.

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